Thionyl Chloride → 1-Benzyl-2-(chloromethyl)pyrrolidinium chloride

Participants

Reaction Conditions

Reaction Steps

(1-benzylpyrrolidin-2-yl)methanol was slowly added to thionyl chloride (45 eq) and the resulting mixture was stirred for 15 h at 35° C. All the volatiles were removed in vacuo. The yellow oil residue was treated with Et2O and re-evaporated to drive off excess thionyl chloride. The crude material was then dried at the high vacuum pump for 2 h to afford the product (100%). 1H NMR (400 MHz, CDCl3) 1.85-2.01 (m, 1H), 2.15-2.32 (m, 3H), 2.85-3.05 (m, 1H), 3.43-3.54 (m, 1H), 3.65-3.79 (m, 1H), 3.92-4.02 (m, 2H), 4.20-4.22 (m, 1H), 4.41-4.43 (m, 1H), 7.44-7.62 (m, 5H).

Provenance & Evidence